Compounds derived from arylacetic acids
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Chapter 9. Compounds derived from arylacetic acids 9.1. Compounds derived from phenylacetic acid 1-(3-Bromo-5-fluoro-2-hydroxyphenyl)-2-phenylethanone [4108-04-7]
C14H10BrFO2 Syntheses
OH Br
mol.wt. 309.13
COCH2
-Preparation by Fries rearrangement of 2-bromo-4-fluorophenyl phenylacetate with aluminium chloride, according to the methods [1313], *without solvent at 130° for 2 h [742]; *in nitrobenzene at 25° for 6 h [742]. -Also refer to: [253].
F
m.p. 130° [253]; b.p.1.5 154-155° [742]. 1-(3,5-Dibromo-2,4-dihydroxyphenyl)-2-phenylethanone [19816-40-1]
C14H10Br2O3 Syntheses
OH Br
mol.wt. 386.04
COCH2
-Obtained by reaction of bromine (2 mol) with 4-phenylacetylresorcinol in acetic acid for 48 h [182]. -Also obtained by Friedel-Crafts acylation of 2,4-dibromoresorcinol with phenylacetyl chloride in nitrobenzene in the presence of aluminium chloride, first at r.t. overnight, then heating on a steam bath for 4 h (44%) [307].
HO Br m.p. 190° [307], 180° [182].
1-(3-Chloro-5-fluoro-2-hydroxyphenyl)-2-phenylethanone [4108-05-8]
C14H10ClFO2 Syntheses
OH Cl
mol.wt. 264.68
COCH2
-Preparation by Fries rearrangement of 2-chloro-4-fluorophenyl phenylacetate with aluminium chloride, according to the methods [1313], *without solvent at 130° for 2 h [742]; F *in nitrobenzene at 25° for 6 h [742]. -Also obtained by Friedel-Crafts acylation of p-fluoroanisole, followed by demethylation and chlorination of the obtained ketone [253]. m.p. 122° [253];
b.p.1-1.5 209-210° [742].
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HYDROXYACETOPHENONES
1-(3,5-Dichloro-4-hydroxyphenyl)-2-phenylethanone [73048-86-9]
C14H10Cl2O2 Synthesis
OH Cl
mol.wt. 281.11
Cl
COCH2
-Obtained by DDQ oxidation of 1-(3,5-dichloro-4-hydroxyphenyl)-2-phenylethanol in dioxane at r.t. for 16 h (82%) [144]. m.p. 132-135° [144];
1H
NMR [144].
1-(4-Bromo-2-hydroxyphenyl)-2-phenylethanone [54981-35-0]
C14H11BrO2
mol.wt. 291.14
Synthesis
OH COCH2 Br
-Obtained by Fries rearrangement of 3-bromophenyl phenylacetate with aluminium chloride in carbon disulfide for 1 h at r.t. [1391]. m.p. 68° [1391].
1-(5-Bromo-2-hydroxyphenyl)-2-phenylethanone [54981-34-9]
C14H11BrO2
mol.wt. 291.14
Synthesis
OH COCH 2
Br
-Obtained by Fries rearrangement of 4-bromophenyl phenylacetate with aluminium chloride in carbon disulfide for 1 h at r.t. [1391]. m.p. 70° [1391].
1-(3-Bromo-2,4-dihydroxyphenyl)-2-phenylethanone [19816-35-4]
C14H11BrO3 Synthesis
OH Br
mol.wt. 307.14
COCH2
HO m.p. 195° [307].
-Obtained by Friedel-Crafts acylation of 2-bromoresorcinol with phenylacetyl chloride in nitrobenzene in the presence of aluminium chloride, first at r.t. overnight, then heating on a steam bath for 4 h (50%) [307].
COMPOUNDS DERIVED FROM ARYLACETIC ACIDS
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1-(5-Bromo-2,4-dihydroxyphenyl)-2-phenylethanone [92152-59-5]
C14H11BrO3
mol.wt. 307.14
Syntheses
OH COCH2 HO Br
-Obtained by reaction of bromine (1 mol) with 4-phenylacetylresorcinol in acetic acid at r.t. for 24 h [182]. -Also obtained by Friedel-Crafts acylation [283] of 4-bromoresorcinol with phenylacetyl chloride in nitrob
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